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Chapter 30
by
Mrwhysper
What's next?
We always know when it’s laid on the line nobody else is as easy to find.
Breakfast was just orange juice and coffee. He and Cass had fooled around for another hour before getting up. She had stroked his cock a bit, but he spent the bulk of the time pleasuring her. He was pretty sure she wasn’t ready for sex yet so he never made a single move in that direction, instead focusing on her, using his fingers and mouth to the best possible effect. He had selfishly given her tits quite a bit of attention, her surprisingly small pink nipples drawing the attention of his mouth, as he enjoyed the way her disproportionately large areolae crinkled and drew up around them when he sucked them to hardness.
In contrast to Kayla, who while she was the very definition of screamer gave little physical sign of climax, Cassie’s orgasms were quiet affairs but her body shook like an earthquake. That she seemed so grateful for those climaxes only pushed Bob to give her more. She had always had attractive features, but she was beautiful when she came.
She had left, giving him a soft sweet kiss goodbye, and as per his new morning ritual he’d hit the shower. By this point, he’d come to expect his clothing laid out, and just like yesterday the room had been redecorated. He wondered if the staff was fucking with him. Today’s ensemble was some lightweight shorts and a muscle shirt. Odd for anything going on at the resort, but then again they weren’t really limited to that, we’re they? He noted that next to his deodorant was a bottle of cologne, and obligingly used a liberal application of it.
Not a bad scent. Cedar and citrus, a note of leather. Whoever picked it shared his tastes.
Going out to the sitting area, he found a small pack, loaded with a water bottle and other outdoor necessities. By the time the knock at the door came he was more confused than ever.
Another sleigh ride, this one alone except for the alt-right dwarf chauffeur, ended at a trailhead in a place he recognized. Long before Matt Stone and Trey Parker named their quiet mountain town, South Park was a fixture in Southwestern Pennsylvania. A historic county park that straddles the border between Bethel Park and South Park Township, it’s home to a wave pool, roller skating park, and miles upon miles of trails. One spot, known as the Stone Manse, was the location the first shots of the Whiskey Rebellion were fired in 1794.
This particular trailhead has a bike rack with a pair of mountain bikes mounted on it, and was familiar to him for a different reason.
“Your fifteenth birthday.”
He turned to see Darlene behind him, effortlessly relaxed and beautiful. The late August sun kissed her skin, making her seem to almost glow with an unearthly light. Her long brown hair teased gently by an errant breeze like something out of an ‘80s teen movie.
“My folks let me pick what to do…”
“And you chose to go biking with me for a whole day. We rode the trails for hours. Then I hit a bump and got thrown from my bike.”
“I was so worried about you…”
“You carried me. For two miles. It turned out to be just a sprain, but you were my hero that day. You’ve always been my hero.”
Bob’s blush covered his ears and tinged his scalp a light crimson. “I was just taking care of the most important person in my life.”
Dar smiled softly. “That was the last time I was here. I never left the Pittsburgh area. I could have come here anytime after I finally got a car, but it didn’t seem right to be here without you.”
That was the last time he’d been there as well. Not for any sentimental reason; life had just happened. Still, when he thought of it, had Charlie… Darlene ever been here without him? Her single mother had never had a car, bussing to her nursing job, often overnight, which the two friends had taken advantage of as it allowed for sleepovers and camp outs throughout their shared youth. His parents had always been more than happy to extend their family to their son’s best friend.
“Enough history. Let’s ride.” Darlene took one of the bikes from the rack and straddled it.
The bike trail, the one they’d ridden on that day more than thirty years prior, was a long twisting affair. And damn if it didn’t feel good to just pedal and coast. Bob even assayed a couple bumps that were on the trail, pulling up into bunny hops before landing lightly and continuing on. He’d led far too sedentary a lifestyle in the past decade, and hadn’t had the thrill of exercise adrenaline coursing through his veins in far too long, so it was exhilarating to experience it again.
Darlene pulled off the trail at a small clearing, so he followed suit. A rough path out of the clearing led to another much smaller one surrounded by a copse of willows. Shady and quiet. The perfect spot for a picnic. More of the show’s magic on display, they found their bags packed with a blanket and a light picnic lunch of thinly sliced rare roast beef sandwiches as well as a bottle of 2015 Argentinian Malbec with a pair of incongruous red solo cups.
“Good year,” Bob muttered as he opened the bottle to breathe. “I never cease to be amazed by what they keep throwing at us.”
The sandwiches where hearty, good San Francisco sourdough with pepperjack cheese and a Gorgonzola horseradish spread, crisp butter lettuce, and red onion sliced so thin you could see through it. Both of them were hungry after the hard ride so they tucked into the sandwiches with gusto. Conversation trended mostly to catching up. Darlene told of her spiral into depression and the horrors of gender dysphoria, while Bob told of the horrors of his failed marriages.
He was pouring the wine when she spoke up.
“That was when I knew.”
She was lying on the blanket, stretched out with her eyes closed, a soft smile on her lips.
“What’s that?” He passed her the red Solo cup and started pouring his own.
She rolled onto her side, propping herself up on one arm, looking at him. “That last trip here. Your birthday. That’s when I knew.”
“All right. I’ll bite. What did you know.”
All right, Darlene. You’ve been wanting this to happen for years. Now or never.
Setting her glass down she stood up and walked to him where he was seated on the blanket. “That was when…” she straddled his lap and slowly lowered herself so that she was sitting in it, eyes meeting his. “I realized…” She leaned in close. She could smell the subtle pairing of the rich meat and dusty wine tannins on his breath. “That I…” she kissed him, quickly, softly, lips just brushing his. “Was in love with you.”
He sat stunned, just staring into her hazel eyes, but not responding.
Fuck. Too fast. Overplayed my hand…
“I… words aren’t enough.” He slipped his arms around her and pressed his lips to hers, kissing her soundly. She felt all the tension drain out of her. Wrapping her legs around his waist, she pressed herself to him, her mouth opening to invite him in and moaning her encouragement as his tongue found hers.
(Title: ‘Friends and Lovers’ by Carl Anderson feat. Gloria Loring)
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Harem Hotel
A reality show to alter reality
A reality show in which contestants compete for one lucky man or woman's affections, and are changed until they can.
Updated on Jun 18, 2026
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Created on Jan 9, 2022
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